HCID 178460016, compound → 1-benzyl-4-(methyl-1,3,4-oxadiazolyl)-4-(N-phenylpropionamido)piperidine

HRID 414236Notes

Reaction equation

HRID 414236 reaction equation
[C:1]([O-])(=[O:4])[CH2:2]C.[CH2:6]([NH+:13]1[CH2:18][CH2:17][C:16]([C:30]2[NH:34][N:33]=NN=2)([N:19]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:20](=[O:23])[CH2:21][CH3:22])[CH2:15][CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(OC(=O)C)(=O)C>[CH2:6]([N:13]1[CH2:14][CH2:15][C:16]([C:30]2[O:4][C:1]([CH3:2])=[N:33][N:34]=2)([N:19]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:20](=[O:23])[CH2:21][CH3:22])[CH2:17][CH2:18]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

3

Reactant 1

HCID 178460016HCID 178460016, compound

Product 1

HCID 147739871-benzyl-4-(methyl-1,3,4-oxadiazolyl)-4-(N-phenylpropionamido)piperidineYield 80%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
110 °C

Procedure

A 100 ml r.b. flask was charged with 1-benzyl-4-(1H-tetrazol-5-yl)-4-(N-phenylpropionamido)piperidinium propionate (6.04 g, 13 mmol) and acetic anhydride (50 ml). The resulting mixture was stirred at 110° C. for 2 hours and concentrated in vacuo. The crude was dissolved in CH2Cl2 (100 ml), washed with 5% Na2CO3 (100 ml), dried over Na2SO4 and concentrated in vacuo. The resulting residue was chromatographed (SiO2, EtOAc/Hex 1:1) to give the product (4.20 g, 10.4 mmol) as a viscous oil: NMR (60 MHz, CDCl3) δ 0.90 (t, 3H, CH3CH2CO), 2.61 (s, 3H, oxadiazolyl CH3), 3.46 (s, 2H, benzyl CH2), 7.33 and 7.52 (2bs, 10H, phenyl H's). ##STR28##

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe crude was dissolved in CH2Cl2 (100 ml)
  3. washwashed with 5% Na2CO3 (100 ml)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was chromatographed (SiO2, EtOAc/Hex 1:1)

Sources & evidence

ORD record
ord-48132d94625a4db88293f69364ca37cd
Source dataset
uspto-grants-1988_12
Patent number
US04791120

Reaction notes

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